Macrocyclic antibiotics are the newest and fastest growing class of chiral selectors for enantiomeric separations. Enantiomeric separation and evaluation are now mandated by the Food and Drug Administration for all pharmaceutical compounds that can exist as racemic modifications. Approximately 75 percent of all pharmaceutical products are chiral. Currently the mechanism(s) by which macrocyclic antibiotics achieve chiral recognition and enantioselective separation is unknown. There are three basic aims/objectives to this proposed work. They are: (1) elucidate the chiral recognition/enantioselective separation mechanism specifically for the glycopeptide antibiotics. (2) Synthesize and evaluate a new type of very simple macrocyclic glycopeptide (note that all known macrocyclic glycopeptides are produced biologically), and (3) Evaluate two unique, anionic-boron containing macrocyclic antibiotics. This work should greatly expand our understanding of these important compounds as well as their utility in the enantiomeric separation of biologically important molecules.